US4144080A - Process for making amine oxide solution of cellulose - Google Patents

Process for making amine oxide solution of cellulose Download PDF

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Publication number
US4144080A
US4144080A US05/819,082 US81908277A US4144080A US 4144080 A US4144080 A US 4144080A US 81908277 A US81908277 A US 81908277A US 4144080 A US4144080 A US 4144080A
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US
United States
Prior art keywords
cellulose
amine oxide
solvent
extruder
tertiary amine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US05/819,082
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English (en)
Inventor
Clarence C. McCorsley, III
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Akzona Inc
Original Assignee
Akzona Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Akzona Inc filed Critical Akzona Inc
Priority to US05/819,082 priority Critical patent/US4144080A/en
Priority to AR272908A priority patent/AR225004A1/es
Priority to ZA00783707A priority patent/ZA783707B/xx
Priority to IN496/DEL/78A priority patent/IN147905B/en
Priority to GR56672A priority patent/GR64549B/el
Priority to BE189077A priority patent/BE868737A/fr
Priority to FI782170A priority patent/FI64657C/fi
Priority to LU79932A priority patent/LU79932A1/xx
Priority to IT25498/78A priority patent/IT1096905B/it
Priority to NL7807421A priority patent/NL7807421A/xx
Priority to DE2830685A priority patent/DE2830685C3/de
Priority to GB787829831A priority patent/GB2001320B/en
Priority to TR20127A priority patent/TR20127A/xx
Priority to AU38147/78A priority patent/AU3814778A/en
Priority to SE7808039A priority patent/SE445926B/sv
Priority to DD78206896A priority patent/DD140356A5/de
Priority to CA000308114A priority patent/CA1116808A/fr
Priority to FR7821985A priority patent/FR2398774A1/fr
Priority to DK330978A priority patent/DK330978A/da
Priority to NO782556A priority patent/NO146987C/no
Priority to BR7804794A priority patent/BR7804794A/pt
Priority to AT0543978A priority patent/AT364900B/de
Priority to JP9203978A priority patent/JPS5424963A/ja
Priority to ES472037A priority patent/ES472037A1/es
Application granted granted Critical
Publication of US4144080A publication Critical patent/US4144080A/en
Priority to US06/136,990 priority patent/US4416698A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
    • C08J3/091—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
    • C08J3/096—Nitrogen containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B1/00—Preparatory treatment of cellulose for making derivatives thereof, e.g. pre-treatment, pre-soaking, activation
    • C08B1/003—Preparation of cellulose solutions, i.e. dopes, with different possible solvents, e.g. ionic liquids
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2301/00—Characterised by the use of cellulose, modified cellulose or cellulose derivatives
    • C08J2301/02—Cellulose; Modified cellulose

Definitions

  • This invention relates generally to cellulose and, more particularly, to a process for making a solution of cellulose in amine oxide, which is adapted to be shaped and precipitated into a cellulosic product such as a fiber filament.
  • a process for dissolving cellulose in a tertiary amine oxide is disclosed in U.S. Pat. No. 2,179,181.
  • a process for dissolving cellulose in a tertiary amine oxide is disclosed in U.S. Pat. No. 2,179,181.
  • from 7% to 10% by weight of cellulose is dissolved in 93 to 90% by weight of a tertiary amine oxide to form a viscous liquid from which the cellulose may be precipitated by pouring or spinning the liquid in water, alcohol, or dilute acid.
  • the tertiary amine oxides suitable for practicing the disclosed process contain 14 or less carbon atoms and may be an oxide of a trialkyl amine or an alkylcycloaliphatic tertiary amine.
  • the resulting solution has the disadvantage of having a low solids content and a high viscosity.
  • two or more different polymers are dissolved in a cyclic mono(N-methylamine-N-oxide) compound and are precipitated together to produce a random copolymer.
  • a diluent such as dimethyl sulfoxide, N-methyl-pyrrolidone or sulfolane may be added to the solution to reduce its viscosity.
  • the solutions may be cast into films or shaped into filaments. As indicated by the Examples set forth in the patent, only low solids solutions can be prepared when cellulose is one of the compounds used in the preparation of the solution.
  • FIG. 1 illustrates diagrammatically one embodiment of an apparatus which may be used in practicing the process of the invention.
  • FIG. 2 shows a modification of the extruder used in the process in which the feed material may be in the form of a slurry and volatile non-solvents can be removed from the cellulose-amine oxide-water mixture before spinning or extruding.
  • a comminuted solid precursor of a solution of cellulose in amine oxide is charged to an extrusion apparatus, is heated to a temperature where the amine oxide dissolves the cellulose to form an extrudable solution of cellulose and the resulting solution is extruded through a die to form an extrudate of substantially uniform composition.
  • the cellulose containing absorbed amine oxide solvent may be comminuted if it is not already in particulate form and charged to the barrel of an extruder where it is heated to a temperature where the cellulose dissolves. The resulting dope is then extruded.
  • the raw material to be used in practicing the invention may be prepared by a process which produces a solid cellulose product containing sufficient amine oxide to dissolve the cellulose simply by heating the product.
  • the cellulose fibers may be swollen by including a non-solvent for cellulose in the amine oxide so solutions of higher solids content than those of discussed prior art can be prepared.
  • the non-solvent may be water or a mixture of water and an organic non-solvent for cellulose miscible with water.
  • the resulting suspension is steeped at such a temperature until the cellulose absorbs amine oxide in an amount to dissolve the cellulose when heated later.
  • the non-solvent or mixture of non-solvent and amine oxide swell the fibers of cellulose facilitating the absorption of the amine oxide and making it possible to prepare a product adapted to be converted with heat into a solution of higher solids than those produced by the prior art process.
  • Any organic non-solvent which has been used must be removed and the water must be reduced to about 1 mole or less per mole of amine oxide. According to said application, this can be accomplished by completing the mixing under a vacuum following by drying.
  • the dried product contains from about 10% to about 40% by weight cellulose, 0 to 20% by weight water and about 90% to 50% by weight amine oxide.
  • the resulting solid product may be comminuted such as by grinding or chopping to form fragments or chips which are stored for immediate or later conversion in accordance with the present invention into a solution.
  • the solid product may now be fed to an extruder and heated to dissolve the cellulose in the amine oxide-water mixture.
  • the resulting solution is then extruded.
  • the preferred temperature range in the barrel of the extruder for dissolving the cellulose is from about 90° C. to about 140° C.
  • the extruder may be operated at any suitable screw speed.
  • the resulting dope is extruded or spun to form a film or yarn by precipitation from the solvent. Precipitation can occur, for example, by deactivating the amine oxide solvent by contacting the extruded precipitate with a non-solvent, such as water.
  • a slurry of cellulose, amine oxide solvent and a miscible non-solvent may be added directly to the extruder where mixing takes place under pressure and heat.
  • the miscible non-solvent may be water or a mixture of water and an organic non-solvent for cellulose miscible with the amine oxide and water.
  • the organic non-solvent and a portion of the water are removed by a vent in the extruder under a vacuum until only the amount of water remains that is necessary to permit dissolving the cellulose in the amine oxide when elevated temperatures and pressure are applied to the mixture.
  • the extruder would not require venting if the precise proportions of cellulose and amine oxide-water are fed directly into the extruder.
  • any suitable tertiary amine oxide which is compatible with water and with the organic liquid which is not a solvent for cellulose may be used such as, for example, those disclosed in the aforesaid patents.
  • the preferred tertiary amine oxides are cyclic mono(N-methylamine-N-oxide) compounds such as, for example, N-methyl-morpholine-N-oxide, N-methylpiperidine-N-oxide, N-methylpyrrolidone-oxide, dimethylcyclohexylamine oxide, and the like.
  • Any suitable aprotic organic liquid non-solvent for cellulose which is miscible with water and will not react with the amine oxide may be used such as, for example, an alcohol, such as methyl alcohol, n-propyl alcohol, isopropyl alcohol, butanol and the like, toluene, xylene, dimethylsulfoxide, dimethylformamide, or the like.
  • an alcohol such as methyl alcohol, n-propyl alcohol, isopropyl alcohol, butanol and the like, toluene, xylene, dimethylsulfoxide, dimethylformamide, or the like.
  • the spun filament may be cooled with air, the surface of the filament wet with water to reduce its tendency to stick to adjacent filaments, and fed through a feedroller to a tension winder.
  • the product may be washed on the spool and skein dried or it can be cut into staple fiber lengths and purified to remove all of the amine-oxide.
  • N-methylmorpholine-oxide containing about 25.27% water is mixed with about 200 milliliters of isopropyl alcohol and heated to 80° C.
  • About 200 grams comminuted wood pulp is added to the resulting mixture and the resulting suspension is steeped until the wood pulp swells.
  • About 400 milliliters of isopropyl alcohol is added and after 10 minutes the isopropyl alcohol and part of the water are removed under vacuum at 60° C. and 27 inches Hg.
  • the water content of the cellulose-amine oxide product is 6%.
  • the resulting cellulose chip product containing amine oxide and water is placed in hopper 10 of extruder 11.
  • the single screw of the extruder is operated at 20 r.p.m. with a pressure in the extruder barrel of about 2000-3000 psi.
  • the temperature in the extruder at the hopper end is about 80° C. and increases through zones of 90° C. and 100° C. to a temperature of 120° C. in metering section 12 near the exit end of the barrel.
  • the necessary heat may be added by conventional means, for example, by electrical resistance wires surrounding the extruder barrel or suitable jacketing for circulating hot water.
  • the cellulose dissolves in the amine oxide and water to form a solution which is extruded through a die 13 or spinnerettes.
  • Cellulose chips prepared in accordance with Example I are placed in hopper 10 of extruder 11 and are extruded at a worm speed of about 20 r.p.m.
  • the temperature in the extruder barrel of hopper 10 is about 100° C. and is increased to 110° C. at which temperature it is maintained through the remainder of the barrel.
  • the cellulose dissolves in the amine oxide-water mixture in the extruder and the resulting dope is extruded through a die.
  • the amine oxide used in practicing the invention may be prepared by oxidizing the amine as described in U.S. Pat. No. 3,333,000; U.S. Pat. No. 3,447,939 or other suitable process.
  • the amine oxide has been referred to herein as simply "amine oxide” but it is to be understood that the amine oxide is always a tertiary amine oxide.
  • Example I a slurry having the same amounts as Example I of the same amine oxide, water and isopropyl alcohol and non-solvent is added to an extruder similar to the one shown in FIG. 1, except that it is fitted with appropriate feed pipes, a mixing blade, and an exhaust vent.
  • the extruder of FIG. 1 is modified to the extent that an inlet pipe or conduit 14 is provided for the hopper 10 to supply liquid or slurry to the hopper 10.
  • a stirring blade is also provided to mix the added materials or maintain the slurry.
  • the extruder barrel 12 is heated to about 100° C.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Textile Engineering (AREA)
  • Dispersion Chemistry (AREA)
  • Biochemistry (AREA)
  • Materials Engineering (AREA)
  • Artificial Filaments (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Extrusion Moulding Of Plastics Or The Like (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Materials For Medical Uses (AREA)
US05/819,082 1977-07-26 1977-07-26 Process for making amine oxide solution of cellulose Expired - Lifetime US4144080A (en)

Priority Applications (25)

Application Number Priority Date Filing Date Title
US05/819,082 US4144080A (en) 1977-07-26 1977-07-26 Process for making amine oxide solution of cellulose
AR272908A AR225004A1 (es) 1977-07-26 1978-06-11 Procedimiento para preparar una solucion de celulosa en un oxido de amina terciaria y procedimiento para elaborar un producto de celulosa
ZA00783707A ZA783707B (en) 1977-07-26 1978-06-28 Process for making amine oxide solution of cellulose
IN496/DEL/78A IN147905B (fr) 1977-07-26 1978-07-01
GR56672A GR64549B (en) 1977-07-26 1978-07-03 Process for making amine oxide solution of cellulose
BE189077A BE868737A (fr) 1977-07-26 1978-07-04 Procede pour preparer une solution de cellulose dans un oxyde d'amine
FI782170A FI64657C (fi) 1977-07-26 1978-07-05 Foerfarande foer framstaellning av formade produkter
LU79932A LU79932A1 (fr) 1977-07-26 1978-07-06
IT25498/78A IT1096905B (it) 1977-07-26 1978-07-10 Procedimento per la preparazione di soluzioni di cellulosa in ossido di ammina
NL7807421A NL7807421A (nl) 1977-07-26 1978-07-10 Werkwijze voor het bereiden van een amineoxideoplossing van cellulose.
DE2830685A DE2830685C3 (de) 1977-07-26 1978-07-12 Verfahren zur Herstellung von Formkörpern aus Lösungen von Cellulose in einem tertiären Aminoxyd
GB787829831A GB2001320B (en) 1977-07-26 1978-07-14 Process for making amine oxide solution of cellulose
TR20127A TR20127A (tr) 1977-07-26 1978-07-18 Selluelozun amin oksid mahlulunun yapilmasi icin usul
AU38147/78A AU3814778A (en) 1977-07-26 1978-07-19 Amine oxide solution of cellulose
SE7808039A SE445926B (sv) 1977-07-26 1978-07-21 Forfarande for framstellning av formade produkter av en losning av cellulosa i en tertier aminoxid
DD78206896A DD140356A5 (de) 1977-07-26 1978-07-24 Verfahren zur herstellung einer aminoxidzelluloseloesung
FR7821985A FR2398774A1 (fr) 1977-07-26 1978-07-25 Procede de preparation d'une solution de cellulose dans un oxyde d'amine tertiaire
DK330978A DK330978A (da) 1977-07-26 1978-07-25 Fremgangsmaade til fremstilling af en aminoxidoploesning af cellulose
NO782556A NO146987C (no) 1977-07-26 1978-07-25 Fremgangsmaate for fremstilling av formede gjenstander av cellulose
BR7804794A BR7804794A (pt) 1977-07-26 1978-07-25 Processo para preparar uma solucao de celulose em um oxido de amina terciaria,e processo para preparar um produto de celulose
CA000308114A CA1116808A (fr) 1977-07-26 1978-07-25 Procede d'obtention de cellulose en solution dans un oxyde d'amine
AT0543978A AT364900B (de) 1977-07-26 1978-07-26 Verfahren zur herstellung einer loesung von cellulose in aminoxid und verfahren zur herstellung eines celluloseproduktes
JP9203978A JPS5424963A (en) 1977-07-26 1978-07-26 Preparation of aminoxide solution of cellulose
ES472037A ES472037A1 (es) 1977-07-26 1978-07-26 Procedimiento para preparar una solucion de celulosa en un oxido de amina terciaria
US06/136,990 US4416698A (en) 1977-07-26 1980-04-03 Shaped cellulose article prepared from a solution containing cellulose dissolved in a tertiary amine N-oxide solvent and a process for making the article

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US05/819,082 US4144080A (en) 1977-07-26 1977-07-26 Process for making amine oxide solution of cellulose

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US06/016,789 Continuation-In-Part US4246221A (en) 1977-07-26 1979-03-02 Process for shaped cellulose article prepared from a solution containing cellulose dissolved in a tertiary amine N-oxide solvent

Publications (1)

Publication Number Publication Date
US4144080A true US4144080A (en) 1979-03-13

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Family Applications (1)

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US05/819,082 Expired - Lifetime US4144080A (en) 1977-07-26 1977-07-26 Process for making amine oxide solution of cellulose

Country Status (24)

Country Link
US (1) US4144080A (fr)
JP (1) JPS5424963A (fr)
AR (1) AR225004A1 (fr)
AT (1) AT364900B (fr)
AU (1) AU3814778A (fr)
BE (1) BE868737A (fr)
BR (1) BR7804794A (fr)
CA (1) CA1116808A (fr)
DD (1) DD140356A5 (fr)
DE (1) DE2830685C3 (fr)
DK (1) DK330978A (fr)
ES (1) ES472037A1 (fr)
FI (1) FI64657C (fr)
FR (1) FR2398774A1 (fr)
GB (1) GB2001320B (fr)
GR (1) GR64549B (fr)
IN (1) IN147905B (fr)
IT (1) IT1096905B (fr)
LU (1) LU79932A1 (fr)
NL (1) NL7807421A (fr)
NO (1) NO146987C (fr)
SE (1) SE445926B (fr)
TR (1) TR20127A (fr)
ZA (1) ZA783707B (fr)

Cited By (78)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4246221A (en) * 1979-03-02 1981-01-20 Akzona Incorporated Process for shaped cellulose article prepared from a solution containing cellulose dissolved in a tertiary amine N-oxide solvent
US4261943A (en) * 1979-07-02 1981-04-14 Akzona Incorporated Process for surface treating cellulose products
US4290815A (en) * 1980-01-28 1981-09-22 Akzona Incorporated Use of co-solvents in amine N-oxide solutions
US4324593A (en) * 1978-09-01 1982-04-13 Akzona Incorporated Shapeable tertiary amine N-oxide solution of cellulose, shaped cellulose product made therefrom and process for preparing the shapeable solution and cellulose products
US4416698A (en) * 1977-07-26 1983-11-22 Akzona Incorporated Shaped cellulose article prepared from a solution containing cellulose dissolved in a tertiary amine N-oxide solvent and a process for making the article
US4426228A (en) 1980-09-13 1984-01-17 Akzo Nv Cellulosic molding and spinning compound with low contents of low-molecular decomposition products
US4581072A (en) * 1982-06-08 1986-04-08 Courtaulds Plc Polymer solutions
US5277857A (en) * 1992-01-17 1994-01-11 Viskase Corporation Method of making a cellulose food casing
US5403530A (en) * 1991-02-15 1995-04-04 Courtaulds Plc Elongate member production method
US5413631A (en) * 1993-05-24 1995-05-09 Courtaulds (Holding) Limited Formation of a cellulose-based premix
US5540874A (en) * 1993-02-16 1996-07-30 Mitsubishi Rayon Company Ltd. Cellulose solution for shaping and method of shaping the same
USH1592H (en) * 1992-01-17 1996-09-03 Viskase Corporation Cellulosic food casing
US5584919A (en) * 1993-09-09 1996-12-17 Korea Institute Of Science And Technology Pelletized pre-dope granules of cellulose and tertiary amine oxide, spinning solution, of cellulose and process for making them
US5589125A (en) * 1992-03-17 1996-12-31 Lenzing Aktiengesellschaft Process of and apparatus for making cellulose mouldings
US5603884A (en) * 1994-11-18 1997-02-18 Viskase Corporation Reinforced cellulosic film
US5607639A (en) * 1993-09-13 1997-03-04 Lenzing Aktiengesellschaft Process for the preparation of cellulose sheet
US5626810A (en) * 1993-10-19 1997-05-06 Lenzing Aktiengesellschaft Process for the preparation of cellulose solutions
US5650112A (en) * 1993-07-28 1997-07-22 Lenzing Aktiengesellschaft Process of making cellulose fibers
US5698151A (en) * 1993-07-01 1997-12-16 Lenzing Aktiengesellschaft Process of making cellulose fibres
WO1997047790A1 (fr) * 1996-06-10 1997-12-18 Korea Institute Of Science And Technology Procede de preparation d'une solution homogene de cellulose a partir de n-methylmorpholine-n-oxyde
US5891375A (en) * 1997-07-24 1999-04-06 Alfacel S.A. Processes for precipitating tertiary amine oxide cellulose solutions containing esters and products made therefrom
US5902532A (en) * 1994-12-02 1999-05-11 Akzo Nobel Nv Process for manufacturing cellulose objects
US5939000A (en) * 1993-05-24 1999-08-17 Acordis Fibres (Holdings) Limited Process of making cellulose filaments
US5948905A (en) * 1995-03-31 1999-09-07 Akzo Nobel Nv Method of producing in water-containing celluose solutions in water-containing tertiary amine N-oxides
US5951933A (en) * 1997-07-24 1999-09-14 Alfacel S.A. Processes for precipitating tertiary amine oxide cellulose solutions containing water soluble polymers and products made therefrom
WO2000023249A2 (fr) * 1998-10-21 2000-04-27 Devro Plc Extrusion de cellulose
US6143884A (en) * 1998-05-09 2000-11-07 Acelon Chemicals & Fiber Corporation Manufacturing process of cellulose viscose with low viscosity
US6177035B1 (en) 1997-04-25 2001-01-23 Lenzing Aktiengesellschaft Method for producing cellulose shaped bodies
US6210801B1 (en) 1996-08-23 2001-04-03 Weyerhaeuser Company Lyocell fibers, and compositions for making same
US6235392B1 (en) 1996-08-23 2001-05-22 Weyerhaeuser Company Lyocell fibers and process for their preparation
US6241927B1 (en) 1997-06-17 2001-06-05 Lenzing Aktiengesellschaft Method of producing cellulose fibers
US6248267B1 (en) 1996-03-06 2001-06-19 Mitsubishi Rayon Co., Ltd. Method for manufacturing fibril system fiber
US6306334B1 (en) 1996-08-23 2001-10-23 The Weyerhaeuser Company Process for melt blowing continuous lyocell fibers
US6331354B1 (en) 1996-08-23 2001-12-18 Weyerhaeuser Company Alkaline pulp having low average degree of polymerization values and method of producing the same
US6409883B1 (en) 1999-04-16 2002-06-25 Kimberly-Clark Worldwide, Inc. Methods of making fiber bundles and fibrous structures
US6440547B1 (en) 1996-08-23 2002-08-27 Weyerhaeuser Lyocell film made from cellulose having low degree of polymerization values
US6488876B1 (en) 1997-06-16 2002-12-03 Lenzing Aktiengesellschaft Composition containing fine solid particles
US20030032705A1 (en) * 2001-08-07 2003-02-13 Otter James William Ethylene terpolymer adhesive for condensing furnace heat exchanger laminate material
US20030225206A1 (en) * 2002-05-31 2003-12-04 Lee Tae-Jung Process of producing highly homogeneous cellulose solution
US6773648B2 (en) 1998-11-03 2004-08-10 Weyerhaeuser Company Meltblown process with mechanical attenuation
US6790527B1 (en) 2003-04-16 2004-09-14 Weyerhaeuser Company Lyocell fiber from unbleached pulp
US20040206463A1 (en) * 2003-04-16 2004-10-21 Weyerhaeuser Company Method of making a modified unbleached pulp for lyocell products
US6833187B2 (en) 2003-04-16 2004-12-21 Weyerhaeuser Company Unbleached pulp for lyocell products
US20050019564A1 (en) * 2003-07-25 2005-01-27 Hyosung Corporation Lyocell multifilament
US20050035487A1 (en) * 2002-01-08 2005-02-17 Stefan Zikeli Spinning device and method having cooling by blowing
US20050048151A1 (en) * 2002-01-28 2005-03-03 Zimmer Aktiengesellschaft Ergonomic spinning system
US20050051210A1 (en) * 2002-02-13 2005-03-10 Zimmer Aktiengesellschaft Bursting insert
US20050066646A1 (en) * 2003-06-30 2005-03-31 Hyosung Corporation Cellulose dip cord produced from highly homogeneous cellulose solution and tire using the same
US20050083466A1 (en) * 2003-10-16 2005-04-21 Yun-Bok Lee Array substrate for in-plane switching mode liquid crystal display device and method of fabricating the same
US20050154093A1 (en) * 2003-06-30 2005-07-14 Ik-Hyeon Kwon Solution containing cellulose dissolved in n-methylmorpholine-n-oxide and high tenacity lyocell multifilament using the same
US20050220916A1 (en) * 2002-01-08 2005-10-06 Stefan Zikeli Spinning device and method having turbulent cooling by blowing
US20060055078A1 (en) * 2002-05-24 2006-03-16 Stefan Zikeli Wetting device and spinning installation comprising a wetting device
US20060076704A1 (en) * 2003-06-30 2006-04-13 Hyosung Corporation Homogenous cellulose solution and high tenacity lyocell multifilament using the same
US20060083918A1 (en) * 2003-04-01 2006-04-20 Zimmer Aktiengesellschaft Method and device for producing post-stretched cellulose spun threads
US20060099419A1 (en) * 2004-11-10 2006-05-11 Hyosung Corporation Method for producing cellulose fiber
US20060144062A1 (en) * 2002-03-22 2006-07-06 Stefan Zikeli Method and device for regulating the atmospheric conditions during a spinning process
WO2006125484A1 (fr) * 2005-05-24 2006-11-30 Zimmer Aktiengesellschaft Procede et dispositif pour couper des fils contenant du nmmo et des fibres coupees de cellulose
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FI64657B (fi) 1983-08-31
DE2830685A1 (de) 1979-02-15
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IN147905B (fr) 1980-08-09
NO782556L (no) 1979-01-29
AT364900B (de) 1981-11-25
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IT7825498A0 (it) 1978-07-10
DE2830685B2 (de) 1980-12-04
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NO146987B (no) 1982-10-04
GB2001320A (en) 1979-01-31
FI782170A (fi) 1979-01-27
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FR2398774A1 (fr) 1979-02-23
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FI64657C (fi) 1983-12-12
JPS5424963A (en) 1979-02-24
SE445926B (sv) 1986-07-28
FR2398774B1 (fr) 1983-09-02
NO146987C (no) 1983-01-12
GR64549B (en) 1980-04-12
GB2001320B (en) 1982-06-16
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IT1096905B (it) 1985-08-26
AR225004A1 (es) 1982-02-15
AU3814778A (en) 1980-01-24
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